Ammonium Chloride → 4-(alpha-Cyano-2-fluorobenzyl)-6-(2-butynyloxy)pyrimidine

HRID 1759925Notes

Reaction equation

HRID 1759925 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]#[N:16].Cl[C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]#[C:27][CH3:28])[N:21]=[CH:20][N:19]=1.[Cl-].[NH4+]>O1CCCC1>[C:15]([CH:14]([C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]#[C:27][CH3:28])[N:21]=[CH:20][N:19]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[F:7])#[N:16]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 67592Benzeneacetonitrile, 2-fluoro-HCID 121376024-(2-Butynyloxy)-6-chloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 225997844-(alpha-Cyano-2-fluorobenzyl)-6-(2-butynyloxy)pyrimidineYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 40 ml of tetrahydrofuran was suspended 4.61 g of potassium t-butoxide, to which 4.44 g of (2-fluorophenyl)acetonitrile was added under ice cooling. Then, a solution of 5.00 g of 4-chloro-6-(2-butynyloxy)pyrimidine in 20 ml of tetrahydrofuran was added at 0° C., followed by stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 6.40 g of 4-(α-cyano-2-fluorobenzyl)-6-(2-butynyloxy)pyrimidine (the present compound (145)).

Workup

  1. extractionextracted three times with chloroform
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16f597241f1e476dbf4af1df9d53790e
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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